Date: Thu, 30 Dec 2010 20:03:35 -0500
From: Andi
Subject: New Years In New York (Transgendered-TV)
Disclaimer: The following story contain explicit descriptions of consensual
sexual activity and are not suitable for reading by anyone under the age of
18, or anyone offended by reading such material. These acts include
bisexuality, cross-dressing and other fetishes and perversions.
This story is pure fiction and fantasy. I encourage everyone to practice
safe sex. The story is the property of the Author. Any feedback would be
greatly appreciated. Thanks.
NEW YEARS IN NEW YORK
My name is Kevin, I am 28 years old and single. I am 5'10" tall, weigh 150
pounds, I have short blonde hair and blue eyes.
It was my first trip to New York. I had recently started a job as a
reporter for a small TV station in Raleigh, NC. I convinced management to
send me to New York to cover the ball drop on News Year Eve.
It was my first big assignment and I was excited and eager to show what I
could do. It was just me and my camera man Robert. The drive up was
uneventful and Robert and I seemed to feel at ease with each other.
We arrived a couple of days early, on December 29, so we could do a couple
of stories leading up to New Years eve. A couple of human interest stories
and maybe a story or two on the history of the New Years eve celebration at
Times Square.
Let me tell you about Robert, he is tall with curly brown hair and brown
eyes, He is in great shape and he is with a different girlfriend each time
I see him away from the station. Robert said he had an Aunt and uncle who
lived on Long Island and that was the reason he wanted this assignment so
bad.
Since Robert was going to stay with his Aunt and cousins, he said that we
only needed to get one hotel room. We arrived at the hotel around 5:30 and
Robert put his suitcase in the room and grabbed his overnight bag. He said
he was taking the subway to his aunts house and would be back around 9 in
the morning so we could scout locations to broadcast from during New Years
Eve.
After Robert left I opened the mini bar and fixed myself a mixed drink of
vodka and orange juice. I sipped my drink and flipped through the channels
on TV. After about an hour I decided to take a long shower. I keep my
body shaved except for the hair on my head.
When I finished my shower I dried off and decided it was time to become
Joanna. That is right, I have been a cross dresser since I was 15. I love
women but there have been a few times I had sex with a man so I guess I was
bi, but deep down I saw myself as a woman when I dressed.
I am sure Robert wondered why I had so many suitcases. Little did he know
that tow suitcases had all of my feminine clothes in it. I started not to
bring Joanna's suitcases with me, but since I would have the hotel room all
to myself I could not resist turning Joanna lose on the Big Apple.
It was almost 6:30 when I started my transformation. The first thing I did
was to slide my pink garter belt up my waist. I always get a tingle when I
feel the garters hit my thighs.
I took out a pair of white silk stockings and sat on the bed. I slowly
rolled the stockings up my smooth legs and attached the stocking tops to
the garter belt. Next came the lacy pink panties with the little bow in
front.
I had to stop and fix myself another drink to settle my nerves. I gulp
this one down and returned to dressing. I hooked the pink lacy bra
together, then turned it around and slipped the straps up my arms. It was
a padded bra and gave me a nice set of 34 C Breasts.
I decided on a short black pleated skirt. I had a very small cock but the
pleats helped me conceal what I did have even when I was hard. I put on a
thin silk blouse that allowed just a glimpse of my pink bra. I thought
about wearing a camisole over the bra but I liked how the bra peaked out
when I left the first two buttons undone on my blouse.
So far so good. I took out my makeup case and put on blush and eye liner,
not to much though. I painted my lips a deep red color. Next I took out
my long red wig and fixed it into place. Then I brushed it out. I looked
into the mirror and saw a fairly attractive red head looking back at me. I
know I would never be considered beautiful but I thought I looked good.
It was time for another drink. I was starting to feel really good. I
slipped on my two inch black heels and when I tried to stand I was a little
light headed. My intention was to just dress up and stay in my room.
At around 8 the phone rang and it was the station Manger calling to make
sure we had arrived ok. She said she could not wait to see the stories we
would do. After I hung up the phone I checked myself in the full length
mirror again. I decided that I looked to damn good to stay in my room. I
mean what would be the harm of getting a drink in the hotel bar?
I put on a silver necklace and the matching bracelet and ear rings. I
grabbed my little black purse, put some tissues, my lipstick, some money
and my hotel key into it and I was ready to go. I checked myself in the
mirror one last time then headed out.
Even though I had been out in public before I was still nervous as I rode
the elevator down to the lobby. People were getting on and off at every
floor but no one pointed and scream so I was starting to relax when I left
the elevator and headed to the bar.
The bar was crowded since so many people were in town for the new years eve
celebration. I made my way to the bar and order another screwdriver. I
set on the stool and checked out the crowd. Some couples were trying to
dance even though the space on the dance floor was limited.
As soon as I finished my drink the bartender brought me another one and
told me that it was from the man at the end of the bar. I looked in the
direction the bartender pointed. Oh my, a very well dressed black man held
up his glass and I tried to give him one of my sexiest smiles. It must
have worked because he came over to me and introduced himself as Steve. In
my most feminine voice I told him my name was Joanna.
Steve was even more handsome close up. He had black hair and it was almost
what I would describe as a buzz cut. He also had a mustache and a neatly
trimmed beard. Steve was over 6 feet tall and it looked like he worked
out.
We tried to talk over the blaring music but he had to stand close to me so
we could hear each other. He was leaning in close telling me how pretty he
thought I was. He also had his hand on my thigh and my skirt was pushed up
exposing my stocking tops. If I had not been so drunk at this point I am
sure I would have pushed my skirt down.
By now Steve was kissing my neck and nibbling on my ear. His hand had
worked up ever farther. If I was not careful he would be rubbing my cock
soon. I was afraid of how he would react if he found out I was not a real
woman. Finally I reached down and stopped his hand.
Steve seemed disappointed but then he asked me to dance. I told him I was
not a good dancer plus the floor was too crowded. He told me he did not
like crowds that much but he wanted to get out of his hotel room tonight.
He then said he was glad or he would not have meet such a beautiful woman.
Then he kissed me. lightly at first but then more passionately and
forceful.
I almost melted in his arms. Maybe it was the alcohol but I found myself
kissing him back. I did not even try to stop him when he pushed his tongue
past my lips. When he started exploring my mouth, I started sucking on his
tongue. he pulled me off the bar stool and to my feet. I felt his hands
caressing my back and then they went to my butt. Steve was squeezing my
ass so hard he was all but lifting me off the floor as we kissed.
He finally broke the kiss and we parted. I reached for my drink and gulped
it down. I guess I started to sway because Steve put his arm around me to
steady me. He told me that he thought I needed some fresh air so he led me
out of the bar. He had his hand around my waist and He never let go of me
because he was afraid I would stumble and fall. I clung to his masculine
body as we left the bar.
Out in the lobby Steve asked me if I wanted to call it a night and have him
walk me to my room or did I want to go to his room and maybe we could get
to know each other better. I just smiled and said I would love to see his
room. We got off the elevator on the fifteenth floor. He finally let go
of me so he could unlocked the door.
Once in his room He sat me on the bed and asked me if I wanted another
drink. I told him that I did not think I needed another drink. I took his
hand and pulled me him to me and told him, "All I need right now is another
kiss."
We started kissing again and soon we were laying on the bed side by side
with his arms around me. He started kissing his way down my neck and soon
he was unbuttoning my blouse.
I was lost in the moment and soon he had my bra undone and was sucking on
my nipples. Between the lust I was feeling for Steve and the alcohol I had
let down my guard so when I felt his hand moving up my thigh I was slow in
reacting.
Before I could stop him I felt Steve's hand on my cock. We both froze. I
was afraid that Steve was going to freak and kick the crap out of me for
leading him on.
Steve sat up and looked down at me. I was all but in tears as I pleaded
with Steve not to be angry. I kept telling him I was sorry. I did not
mean to mislead him. I had not intended for it to go this far.
Steve had still not said anything yet. Finally he just smiled, shrugged
and leaned down to kiss me again. When he broke the kiss, he took me into
his arms and pulled me tight. He told me that he had never ben with
someone like me but that he was open minded.
He smiled again and said "You make a beautiful woman and you turn me on, I
hope I did not ruin the moment."
I let out a sigh of relief and started to slide down the bed. First I
removed his shoes and sock, then I undid his belt. As I did this he pulled
his shirt up and off. I unbuttoned and unzipped his trousers and pulled
them down his legs and off. He did not have on any underwear and his semi
hard cock looked delicious so I kissed the head.
He moaned as I sucked the head into my mouth and started sucking hard. As
I sucked the head I reached down and started squeezing his heavy balls.
I let the cock slip from my mouth and started licking the shaft. I licked
down and started sucking on his balls, causing Steve to start moaning. By
now Steve was rock hard and his cock was over 7 inches long and thick.
I gave his balls one last kiss then took the cock back into my hungry
mouth. I was taking all 7 inches and thought Steve would enjoy cumming in
my mouth so I prepared to swallow a load of cum.
Steve had other ideas, He pushed me off of his cock and the he forcefully
turned me onto my stomach. When he pushed up my skirt and ripped my
panties from my body I knew what he wanted and I started begging Steve to
slow down and to let me get some lube. He ignored my pleas as he shoved a
pillow under me so that my ass was in the air.
He spread my ass cheeks with his hands and rammed his cock into me in one
swift motion. I am sure that if they were anyone in the adjoining rooms
that they heard my scream.
He pulled out until all that was left in me was the head of his cock. Then
he rammed it deep again this time only stopping when he had all seven
inches in me.
He kept muttering how tight my sissy cunt was as he started to fuck me in a
slow rhythm. Maybe the liquor had dulled my senses because the pain
quickly went away and I felt a fire start deep inside of me.
As Steve started fucking me hard and rough I reached under me to squeeze
the head of my own cock, I knew it would not be long until I came.
I could not resist the feeling any longer and shot a load of cum onto the
sheets underneath me. Steve continued to fuck my butt for several more
minutes. Suddenly he shoved his big cock into me and held it there
shooting his load deep inside of me.
After he came, Steve collapsed on top of me, we both lay there catching our
breath for a few minutes then I felt Steve pull his cock out of me and I
felt empty.
I felt Steve slap my butt hard as he told me to roll over. I rolled onto
my back and Steve worked his way up to straddle my chest pinning my arms
under him. He put his hand behind my head and pulled my mouth to his slimy
cock.
I was forced to suck and lick his cock until it was clean. When he was
satisfied that I had cleaned his cock properly He held my head in place and
started to fuck my mouth. He did not care how much I gagged as he
continued to force his cock in and out of my mouth.
He was breathing hard and it surprised me when he pulled his cock from my
mouth and started cumming on my face. When my face and neck was covered in
cum he got off of me and went to the bathroom and relieved himself, I was
not sure what to do but I found my ruined pair of panties and used them to
clean the cum from my face.
When Steve returned he couldn't look me in the eyes, finally he tried to
apologize, he kept saying he was sorry for the way he had acted, he did not
know what came over him.
I went to him and put my arms around him. I whispered in his ear that it
was ok. I kissed his cheek and told him that sometimes I loved it rough
and I thought it was hot what we did. He seemed relieved. I think he was
afraid I was going to scream rape or something. We made out for a little
bit longer then I went to the bathroom and cleaned up as best as I could.
My makeup was ruined but I did manage to touch up my lipstick.
I got dressed and kissed Steve one more time as he walked me to the door
and gave me a good bye kiss, he said he was glad he got to have some fun
tonight because he was leaving tomorrow morning for San Francisco on
business.
I was still a little tipsy but I managed to get back to my room without
incident. I decided to shower again. When I was done I took out my
favorite pink lace teddy (I really love pink lingerie) and fixed myself
another drink. It was still early so I laid on the bed and watched some
cheap porn on the TV.
I figured I would set the alarm clock to go off around 6 so I could change
and hide all evidence of Joanna before Robert came back to the room.
Between the drinks and the wild rough sex with Steve I was exhausted and
drifted off to sleep. So imagine my surprise and shock when I was awaken
from the sound of someone laughing. I glanced at the clock and seen that I
had slept straight through the night and it was already 9 in the morning.
At some point I had rolled over onto my stomach. I just wanted to bury my
face in the pillows and hope that it was a bad dream. I knew it was no
dream when Robert quit laughing.
I heard him say, "Nice ass Kev, I did not know you were a sissy fag who
wore lingerie."
I did not answer Robert but I sensed him coming closer, then I felt him
swat my ass, not hard but enough to get my attention.
I finally rolled over and faced him. I knew my face was bright red from
embarrassment. "Please do you have to speak so mean to me? I will go
change and we can forget any of this ever happened."
"I do not think you are in any position to ask for any favors, I wonder
what the station manager will think when I tell her?"
"Oh God Robert, please I am begging you, don't tell anyone, PLEASE!!"
He gave me a lecherous grin,"I tell you what, maybe we can work something
out and no one will need to know."
"Thank you, Thank you, Thank you, I knew you were a good guy, I will go
change right now."
I thought he was going to let me off the hook. How wrong I was.
"Stop right there, I did not tell you that you could go change."
I froze in place.
"Turn around for me and do it slowly. I want to see your outfit."
I took a deep breath and did a slow 360 degree turn.
"Not bad, now go set on the bed for me."
Please Robert can't we just get to work and put this behind us?"
"You will do as I say or I will expose your secret to everyone at the
station, you know how word gets around in this business I doubt if you
would ever get another job anywhere in the country."
I looked at the floor and mumbled a weak "Yes Sir."
I went to the bed and sat down. I was told to lean back and spread my
legs. Then I had to start rubbing my cock through the lace of the teddy
like I was rubbing my pussy and clit.
Robert then made me pull my cock free of the material and star stroking it.
First he laughed at how small it was then He asked me what did I do last
night and I told him I went to the bar.
"You went dressed as a woman right?"
"Yes Sir."
"Did you get hit on by any guys?"
"Just one."
"Did you leave the bar with him?"
I nodded yes.
"Where did you go?"
"To his room."
Robert ordered me to lay on my side and continue to stroke my cock with one
hand while I reached behind me and start pushing a finger inside my ass.
As I pushed a finger into my ass Robert must have seen me flinch because he
asked did it hurt. I told him it did.
"Why? Did you get fucked last night and your ass is sore this morning?"
I thought I was going to die from the humiliation but I managed to answer
him.
Robert made me tell him all the details from last nights encounter as I
laid there, jacked off and fingered my sore ass.
"I see your small cock is rock hard, are you ready to cum?"
"Yes Sir I am very close."
"OK you may Cum but when you do you had better catch every drop and lick
your hand clean."
I think I started shooting before he finished the sentenced, I did as I was
told and caught all my cum in my hand and when I stopped cumming I raised
my hand to my lips and licked up every drop.
"Good little cum slut. Now go get dressed we have work to do. I am sure
you have panties and pantyhose to wear under your male clothes, don't
disapoint me."
When I was dressed and had returned to the room, Robert made me undo my
pants and show him the tan pantyhose and red panties that I had on.
We walked around New York and shot some footage. I did a few interviews of
people on the street, asking them if they were going to be in Times Square
when the ball dropped and what were their resolutions for the new year.
We finished work for the day and had a quick snack at a local Deli that
Robert liked then headed back to the room. When we entered Robert asked me
where were the feminine clothes that I had brought to New York with me.
I pointed out the two suitcases and he started to go through them. He laid
out a black corset with garters, black stockings, black lace panties and my
very snug little black dress.
He said he would start editing and for me to go get fully dressed, makeup,
wig, the works and he had better be impressed or I would not like what
might happen. I started to argue but decided what was the point.
It took me almost 45 minutes to dress and do my makeup but when I entered
the room Roberts jaw almost hit the floor. I guess I looked a lot better
than he thought I would.
Robert recovered, "Not bad sissy bitch, get over here and see if you
approve of what I have done. As I stood beside Robert and watched the
video, he reached out and started feeling of my ass. He started to roughly
squeeze my butt cheeks through the thin material of my dress.
I managed to tell him that he did a great editing job and I sent the file
over the Internet to the station in Raleigh. I hoped that with our work
done for the day that Robert would leave and go back to his Aunts place.
Robert had other plans. As soon as the file was uploaded, he stood up and
started unzipping his pants. He pushed them and his underwear down to his
thighs and exposed his semi hard cock. In the state that it was in it was
still 6 inches long.
I was ordered to kneel in front of him and give him my best blow job. As I
kneeled between Robert's legs and slowly started to run my hand up and down
his cock, I thought to myself that this was not to bad, Robert was a good
looking guy with a nice size cock. I quit worrying about what would happen
later if Robert decided to tell someone about me and threw myself into the
job at hand.
First I started planting sloppy wet kisses up and down the shaft of his
cock. Then I licked the underside of the shaft. By now his cock was
completely hard and was probably close to nine inches. No wonder Robert
did so well with women.
I took his cock into my mouth and started to suck it. I kept my hand at
the base of his cock as I started working my mouth up and down the shaft.
Each time I went down I would take more and more of his cock and when I
pulled back you could a dark red ring from my lisp tick where I had
stopped.
I was not able to take all nine inches into my mouth but I did manage at
least seven. Robert must have been enjoying himself because he had his
head back and his eyes closed. He was emitting soft moans of pleasure.
Robert had stamina and it took over twenty-five minutes of me sucking his
cock before I felt a hand at the back of my head forcing me to suck harder
and bob my head up and down faster.
I was rewarded for all my hard work when Robert gave a loud grunt and shot
a huge load of cum into my mouth. I felt strand after strand hit the back
of my throat forcing me to swallow as fast as I could. Still there was so
much that some dribble out of the corners of my mouth and down my chin.
Robert finally let go of my head but I continued to milk his cock with my
mouth. He eventually pushed me away and told me to go touch up my makeup,
we were going out to diner.
After I made myself presentable again, we went down and caught a taxi.
Robert told him the address of the restaurant and we pulled away. Robert
pulled me close and I rested my head on his shoulder and I felt Robert's
hand on my thigh slowly caressing the bare skin just above the stocking
tops.
He said that he had not thought to ask if I had a feminine name I went by
because he did not think calling me Kevin, bitch, slut or whore in public
was a good idea. I told him it was Joanna.
We arrived at a fancy French restaurant and I asked Robert how would we
ever get in since a place like this would be booked up weeks in advance,
especially over the holiday season.
Robert just smiled at me and said he had a plan. His cousin was the head
waiter for the place but it may take more than that. I was enjoying being
out on the town as Joanna and I was busy taking in al the sights and sounds
of New York so I did not think anything about it and just figured he would
have to bribe him a little.
When we entered Robert introduced me to his cousin Richard and asked if he
could squeeze us in. Richard said he would try but it might be a while.
Robert leaned in and whispered something in his cousins ear and when he
did, I caught Richard's eyes going up and down my body.
Richard grinned and said he thought he could work something out. It turned
out that Richard had more pull that I thought he did because soon Robert
and I was seated a romantic table tucked into the back corner of the
restaurant. It was very secluded, no one passed by.
It was a lovely meal and Robert was an exceptional conversationalist. I
was almost convinced I was on a real date. It was almost time to order
desert when Richard came by our table.
He stood right next to me and got very close. I heard him ask Richard if I
was ready to do it. I looked at them both and asked, "do what?"
Robert gave me one of those looks and said that part of the deal was that
if Richard got us in I would give him a hand job. I think Richard expected
me to say no or at least resist a little. I thought a hand job for a great
evening was a spectacular deal so I smiled up at Richard and asked him
where he wanted to do it.
He glanced around and quickly unzipped his fly. I reached out to fondle
his cock and squeeze the head. He was already hard as I started working my
hand up and down the shaft. He was nowhere near as big as Robert or Steve
for that matter but it felt good in my hand.
Richard was enjoying the hand job but it was taking him way to long and I
was afraid someone would see what I was doing so I decided to hurry things
along, I leaned down and gave the head of his cock a few good licks, then
took the head into my mouth as I quickly worked my hand up and down the
shaft. I thought Richard was going to collapse when he started cumming.
He managed to stay on his feet. I liked his cock clean then tucked it back
into his pants and zipped him up just as the waitress brought our dessert.
She caught me pushing a errant drop of his cum into my mouth and the look
on Richard's face. As she set my chocolate moose in front of me she winked
at me and said that she hoped I enjoyed my desert as much as I had enjoyed
Richard.
Richard over heard her and slapped her playfully on the butt and told her
to mind her own business. They both were laughing as they left the table.
Later during the cab ride back to the hotel, Robert said "You really enjoy
being a woman don't you?"
I told him I enjoyed it a lot, and this had already been the most exciting
couple of days of my life and we still had at least one more day and night
left in New York, even if we were working tomorrow night.
Robert hugged me and told me that tonight was not over yet. When we got
back to the hotel we stopped at the bar for a couple of drinks, I was not
going to over do it like the night before so I ordered a black cherry
Mojito and nursed my drink as I watched the people.
Robert even managed to pull me onto the small crowded dance floor and held
me in his arms as we danced to a slow song. We started kissing and I felt
his hands back on my ass as we danced. I started to grind my body against
his already hard cock.
Soon after that Robert asked me if I was ready to go back to the room. I
told him I had been ready. He responded by telling me I was a good little
whore.
Roberts hands were all over me while we were in the elevator. When we
reached our floor the doors opened and they were two couples waiting.
After they had got on and the doors were closing I heard the cute blonde
say "He is going to get very lucky tonight" and they all laughed.
By now all pretense of Robert "forcing" me to do things were out the
window, it was obvious to both of us that I wanted to be Roberts slut and
would do anything to please him.
Back in the hotel room we kissed frantically as our passion over took us.
I broke the kiss and smiled up at him then started to slowly undress
Robert. I slide his jacket over his shoulders and off. Then I pulled his
shirt from the waist of his pants and as I pulled it over his head and off
I kissed his flat tummy then kissed and nibbled at his right nipple.
I undid his belt, unbuttoned his pants and let then gather around his
ankles. He lifted his right foot then his left foot as I removed his
shoes, shocks and slipped his pants off his body.
His hard throbbing cock was at eye level and I could not resist kissing the
slit then sucking the head for a few moments.
"Baby slut, that fells good but that is not what I want right now."
I let his cock slip from my mouth, pushed him back and he fell onto the
bed. As he watched, I stood up and started doing a slow sexy dance for
him. As I danced I reached down and took the hem of my dress and slowly
raised it exposing first my panties, them my corset eventually lifting the
dress over my head and throwing it onto a chair in the corner.
I turned my back to Robert and wiggled my ass as I slide the panties down
and off. I reached behind me and spread my ass cheeks as I looked over my
shoulder and sexily licked my lips.
Then I said in my most feminine, most sexy voice, "Please Robert, will you
make love to my tight sissy ass? Will you fuck me hard and deep and make
me your bitch?"
Robert seemed to think that was a great idea because he jumped off the bed
and forced me down onto my hands and knees on the hotel floor.
before I could protest, I felt the head of Robert's hard cock pressed
against my anal ring. Like Steve, Robert entered me with one hard thrust.
Again it hurt but I bit my lower lip and managed not to cry out in pain.
Robert did try not to be to rough, well at the beginning anyway. Soon he
was ramming his rock hard cock deep into me and I felt his heavy balls
slapping against my ass.
Robert surprised me when I felt his hand on my small cock. As he fucked me
he started to stroke my sissy clit. I felt it build inside of me and soon
I came hard.
He continued to fuck me hard before he came. When he finished shooting cum
deep inside me we both collapsed on the floor. We were both covered in
sweat but my sweat was mixed with cum.
After we regained our strength we crawled into bed and feel asleep. I
awoke early the next morning with my back to Robert, he had his arm around
me and I could feel the head of his cock nestled between my ass cheeks. I
don't know what he was dreaming about but he was already rock hard.
I managed to move his arm and crawl out from under him without waking him
up. I went to the bathroom to clean up and when I returned Robert was on
his back snoring lightly. The sun was not up yet and I did not want to
wake Robert up but I could not resist. I bent down to take his cock into
my mouth again. I had planned to give Robert a nice slow blow job, but
after seeing that beautiful cock sticking up I got a better idea so I
crawled onto the bed and straddled Roberts cock.
I reached behind me and spread my ass cheeks again. Robert was a heavy
sleeper but he woke up when I lowered my ass onto his cock. I slowly sank
down until I had all nine inches in me. I sat there a few seconds and
enjoy the feeling of being full.
As I started to rise up and down on Robert's cock, he reached up and
started playing with my nipples. The faster I rode up and down on his cock
the harder he pinched and twisted my sensitive nipples. Between the cock
in my ass and the feeling of my nipples being manipulated I could not help
it when I shot a load of cum onto Roberts belly and chest.
When I came, the contractions in my ass milked the cum out of Robert and he
shot his second load of the night into my ass. I apologized for coming on
him but Robert said it was ok, as long as I licked it clean.
First I licked the shaft and the area around the base cleaning his
cock. Then I licked my way up cleaning off his belly then his chest. I
could not resist nibbling his left nipple before I finally rested my head
on his chest.
That is how I feel asleep as Robert covered our bodies with a sheet.
______
The next morning as we were getting ready to head out to do some more
interviews and take some footage of the preparations for the nights
celebration my cell phone rang and it was our station manager.
She said she had some bad news, the station owner refuse to pay for the
satellite feed so our live broadcast had been canceled. She told me to do
a couple more human interest stories if we could find them, then we could
head home tomorrow.
I was disappointed but when I told Robert he just took the news in stride.
He gave me one of those sexy grins of his and said it was cool, we could
just go to the countdown and enjoy ourselves and not worry about having to
do a broadcast.
We spent the day doing more interviews, mostly we focused on police
officers and firemen, reporting on the security plans and procedures.
After we finished filing our reports it was still early so I asked Robert
what he wanted to do. He said he wanted to see what Joanna was wearing to
Times Square. I told him I had only brought the little black dress from
the night before and a black pleated skirt.
We were running low on money so there was no high priced fancy restaurant
tonight. So while he ordered a pizza I went to become Joanna once again.
When I emerged from the bathroom and did a quick spin showing off my
outfit, Robert said he really liked the stockings and pink bra showing
through my blouse.
After the last few days I had become more efficient in my transformation so
I was done before the Pizza arrived. I had put on the outfit I had worn
the first night in New York except that this time I had on a pair of white
panties instead of pink.
As we ate Robert asked me questions about how old I was when I started
dressing up, how did I get started, who was the first guy I dressed for ad
had sex with all really personal questions.
Robert surprised me by saying that he and two of his closest friends
experimented when they were in their teens. He never did more than give
several hand jobs to his friends but that they went as far as sucking his
cock.
When their was just one piece of pizza left Robert asked me if I wanted it,
I told him no he could have it and that I wanted desert. As he ate his
pizza, I slide to my knees. When we returned to the hotel room Robert had
changed into a pair of lose fitting shorts so it was easy to free his cock.
I took it into my mouth and proceeded to give Robert a nice long blow job
and was rewarded with a mouth full of delicious cum. I savored the taste
as I swallowed. I think I was becoming addicted to cum.
After we finished eating and I touched up my lipstick it was around 8:30.
Robert called his cousin Richard and asked if he was going to Times Square,
he said he was so Robert told him what hotel we were in and to come by here
first. We could all have a few drinks in the bar before we headed out.
Robert and I was sitting in a corner booth when Robert and another guy
walked in, I later found out that it was Richards little brother Brad.
We had several beers then decided to join the crown in the streets. It was
unseasonably warm so I was able to wear a light leather jacket over my
short skirt and thin blouse.
Times Square was packed with close to a million people. There was no way
we could get close to the center of activity but we managed to squeeze into
a spot where we could at least see the ball drop.
People were blowing horns and laughing, everyone was having a great time.
I felt my skirt being lifted up from behind and as I looked back I heard
Robert telling his cousins what a sexy tight ass I had. I tried to push my
skirt back down but they would not let me, soon each man took a turn
pinching and squeezing my ass through my panties.
Robert spun me around and started kissing me, his hands went back to my
ass. We made out for several minutes and then he passed me to Richard.
Richard kissed me deep and passionately and he too took the chance to play
with my ass.
I felt Brad nudge Richard and tell him he wanted a turn. Richard passed me
to Brad and he took me into his arms, Where Richard was passionate, Brad
was more forceful and aggressive. As we kissed I felt Brad squeeze my ass
hard, I even felt his finger nails dig into my flesh.
After several minutes we came up for air. I realized that several people
were watching us and I was embarrassed. I straitened my skirt and told
Robert that I was getting cold, he pulled me into his arms and we snuggled
close and kissed occasionally.
Richard whispered something into Roberts ear and from the look on Roberts
face I knew they were up to something. Brad watched us closely as Richard
pulled my to him and told me to grind my ass into his crotch.
When I did I felt that he was rock hard. I looked back over my shoulder to
see Richard undoing his zipper. When he had his cock out he flipped my
skirt up again and slide my panties to the side.
I could not believe what was happening, I was going be fucked in public in
the middle of Times Square. Richard pushed forward and the head of his
cock push past my anal ring.
He went slowly at first but I think he was either afraid I would make him
stop or that we night get caught because he started fucking me hard and
rough. The crowd was loud so just those close by heard the grunts Richard
was making each time he drove into me.
I felt Richard's balls press against my ass and I knew Richard was as deep
in me as he was going to get. He kept his cock deep inside me and started
shooting his load.
Richard quickly pulled out and zipped up. He pushed me over to Brad and he
unzipped his pants and positioned himself behind me. Brad grabbed my hair
and pulled me back to him, I was glad that it held in place.
Brad entered me forcefully and started fucking me. I had not seen Brad's
cock but it felt bigger than Richard's but smaller than Robert's. He was
pulling my hair and calling me dirty names. Our actions were attracting a
lot of attention from the people around us. the women acted like they were
disgusted but the guys seemed to be enjoying the show.
Suddenly I could not hold back any longer and coated my panties with cum.
I was lost in my own orgasm and did not realize that Brad was done and
pulling out of me.
When Brad was finished, he acted embarrassed and Richard told Robert that
they were taking off and left. I gave Robert a hurt look and asked him how
he could pass me around like a sex toy.
Robert took me into his arms and told me to quit acting like I did not
enjoy what had happened. I tried to pull away but when Robert gave one of
his patented grins I could not stay mad so I did what I thought was best.
I kissed him and started sucking on his tongue when he pushed it past my
lips.
There were 25 minutes left before midnight and Robert spun me around. my
ass was well lubricated by two loads of cum so Robert's large cock entered
me easily. Robert fucked me slowly as he reached around to cup my breasts
through my padded bra and blouse.
He would fuck me for a few minutes then stop and leave it buried in my ass.
I started wiggling my ass to encourage him to finish. I was afraid someone
would eventually call the cops on us.
As Robert groped my breasts he kissed my neck them whispered into my
ear. "Most couples want to share a kiss at midnight, If I time this right,
we will share an incredible cum when the clock strikes 12."
As midnight approached Robert had to stop several times to keep from
cumming to soon. He would nibble on my ear and squeeze my breasts. He
slid his hand under my blouse and started pinching my nipples through my
bra.
At 3 minutes to midnight Robert started fucking me in earnest. He started
fucking me harder and harder, when the time hit 1 minute to midnight I
started pushing back to meet his thrusts. I forgot about the people around
us, all I could do was concentrate on the pleasure in my ass.
I was brought out of my haze when everyone around me started counting down.
10..9..8...
We fucked faster and faster....
7...6...5...
I tried, really I did. but I could not help it and my orgasm hit me with
two seconds left. I was still cumming and the waves of pleasure were going
through my body as at the stroke of midnight Robert emptied his balls deep
in my ass.
If Robert did not have his arms around me playing with my breasts I would
have collapsed. His cock was still in me as he pulled me to a nearby wall
and we leaned against it until we could recover. All I could think about
was that if tonight was any indication, the new year would be incredible.
When Robert's cock finally went soft and slipped from my well fucked ass, I
could feel cum running down my thighs. Robert finally turned me around and
looked into my eyes, wished me a Happy New Years then we shared a long deep
passionate kiss.
We hung out and watched the people and kissed occasionally. Around 2
A.M. we made it back to our room. We were both exhausted so I changed into
a pink nighty and we cuddled before going to sleep.
The next morning I packed Joanna away in her suitcases and became Kevin
again. I still wore a pair of panties under my clothes but it was not the
same.
Robert noticed how quiet I was on the long drive home and asked me what was
wrong. I told him how much fun I had while in New York and that I could
not go back to living the way I did before our trip.
Robert told me he would be sure to make Joanna's life fun and exciting in
the future. I did not have on feminine clothes, makeup or a wig but I
still felt all sissy and dainty as I rested my head on Robert's shoulder.
I thought all of our fun was over but somewhere in Maryland Robert pulled
into a truck stop for gas. When he had filled up the gas tank he pulled
into a deserted part of the parking lot and stopped.
He said he had to get something out of the trunk. I didn't think much
about it until Robert returned and handed me a bundle of clothes. It was
my pink bra, garter belt and a pair of black stockings. He told me to get
into the back seat and get dressed.
I knew better than to argue with him, besides I was starting to like the
idea of sex in public. He stood outside of the car while I dressed. I did
not bother with the wig but I did apply a dark red shade of lipstick. When
I was done I knocked on the window and he got in beside of me in the back
seat.
Robert slide his pants and underwear down and without a word he put his
hand behind my head and pulled my mouth toward his crotch. I knew what he
wanted and eagerly started sucking his cock.
He must have been tired because he took forever before he gave me what I
wanted, what I realized I needed. He shot a big load of hot cum down my
throat.
I nursed his cock until it got soft then I redressed in my male clothes. I
kept on the lingerie underneath.
A week after our trip I heard through the grapevine that Robert had broken
up with his latest girlfriend. She had found evidence that Robert had
hooked up with someone while in New York.
Robert and I continued to see each other and within a month he had moved
into my apartment building. He got a place two floors above me.
I seldom stay in my own apartment, as soon as I get home from work I would
become Robert's girlfriend and love slave Joanna. We are both very happy.
The End
___________
Again, any comments would be greatly appreciated.